With iTunes 7, you can now transfer purchased tracks (ie, those purchased from the iTunes Store) from your iPod back to your computer. This includes both traditional DRM-protected iTunes Store tracks as well as the newer “iTunes Plus” DRM-free tracks. Note that iTunes 7.3 or later is required to transfer iTunes Plus tracks.

Unfortunately, this is presently an all-or-nothing deal—there’s no way to transfer back specific purchased tracks on an individual basis. Rather, this option will transfer back ALL purchased tracks that the current iTunes library is authorized to play (and that do not already exist in the iTunes library).

To use this feature, the computer you are transferring the purchased tracks to must first be authorized with the same iTunes Store account that was used to purchase this content in the first place. If you are setting up a new iTunes library, you can ensure that it has been properly authorized by selecting Authorize Computer from the Store menu in iTunes, and then entering your iTunes Store account user name and password.

Once the computer has been authorized, the “Transfer Purchases” option can be used to copy any purchased tracks that are on your iPod but not in the current iTunes library back to your computer. This option can either be found on the iTunes File menu, or by right-clicking on your iPod in the iTunes source list and choosing it from the context menu:

If you are connecting your iPod to a new iTunes library, the automatic sync warning shown earlier will actually show “Transfer Purchases” as an additional option:

In this case, clicking the “Transfer Purchases” button will transfer any purchased content from your iPod instead of performing an automatic synchronization. Once the purchased music has been copied back to your iTunes library, the iPod will remain connected, but no automatic sync will run.

Further, if you find yourself in a situation where you’ve accidentally removed some purchased tracks from your iTunes library, you don’t need to worry about overriding the automatic sync process—iTunes will detect that there are purchased tracks on the iPod that are not present in your iTunes library, and notify you of this, asking you what you want to do about it:

Selecting “Transfer” will naturally transfer those purchased tracks that are missing back into your iTunes library. On the other hand, if you’ve deleted these purchased tracks intentionally, the “Don’t Transfer” option should be selected to erase these tracks from your iPod as well.

Note that metadata such as ratings and play counts for these purchased tracks will also be transferred from your iPod to your iTunes library as part of this process.

Ultimately this feature can be useful for recovering a few purchased tracks at a time, and may even be useful for disaster recovery for users with relatively small iTunes libraries containing only a handful of ripped CDs and some purchased tracks. Since any CDs you own can be re-ripped into your iTunes library, and purchased tracks can be transferred back from your iPod, this feature offers a reasonable compromise for people with small libraries that only consist of these two types of content.

Further, this feature can also provide a very useful way to transfer purchased iTunes tracks between more than one authorized computer. Simply connect your iPod to the second computer and select the “Transfer Purchases” option to reverse-sync your purchased music from your iPod. For those users who keep all of their purchased music on their iPod, this can provide an effective way of keeping all purchased music in sync between two or more iTunes libraries.

Purchases made on the device…

If you’re using an iPhone, iPod touch or Apple TV, you can actually purchase content directly on these devices themselves, either through the iTunes WiFi Store (iPhone and iPod touch), or through the various store menus on the Apple TV 2.0 interface (note that Apple TV v1.x did not allow for purchasing content directly from the device).

The good news is that you don’t need to worry about transferring this content back manually by using “Transfer Purchases.” When you sync one of these devices with your iTunes library, it will automatically detect any content you’ve purchased on the device and transfer it back for you automatically. As an added bonus, device-specific “Purchased” playlists are created to help you keep track of this:

These work in much the same way as the default “Purchased” playlist. If you don’t want them kept around, you can delete them yourself and they will automatically be re-created the next time any music is purchased on another device and transferred back to iTunes.

The Brute-Force Approach—Copying your Media Back Manually

As described previously, with the traditional iPod models your media content itself is actually just copied to your iPod as an external hard disk, and stored in a hidden directory on the iPod itself. This means that for the more experienced and/or adventurous users, you can actually copy your tracks back manually from your iPod to your computer simply by accessing it as an external hard disk.

Note that if you’re not the sort of person who is comfortable working within the innards of your file system, then feel free to skip this section and move on to the Third-Party Software section below.

Keep in mind that this will not work with the iPhone or iPod touch, as these do not connect to the computer as an external hard disk. If you’re an advanced user and you’ve specifically jailbroken your iPhone or iPod touch, then you can access the file system using other tools such as an SFTP client and you will find that the content is stored in much the same way as it is on traditional iPod models. However, this is a more advanced discussion beyond the scope of this tutorial. The use of iPhone or iPod touch compatible third-party software tools is generally much simpler than trying to recover content manually from these devices.

The downside to this approach is that this will not allow you to retrieve iTunes-specific information like playlists, ratings, play counts, skip counts, last played dates and last skipped dates, but you will be able to get back the media files themselves, complete with the important identifying tag information contained within them.

Another consideration is that these files are not well-organized, so it’s not going to be a practical approach for somebody looking to retrieve a specific set of tracks, such as an entire album. The name and file-system structure on the iPod itself is intended to only be used by the iPod and iTunes, and is therefore not organized in any way that would be meaningful to a human.

The bottom line is that this approach is best used in a disaster-recovery scenario, where you want to retrieve ALL of the content from your iPod, and are not particularly concerned about playlists, ratings, play counts, and last played dates.

Further, since most of the third-party applications that we will be discussing later on require access to the iPod’s internal database, this method may be the only way to get your content back off your iPod in the event that the iPod’s internal database has become erased or corrupted. In many cases, an iPod that suddenly shows NO music content on the iPod screen itself, but still shows storage space being taken up when connected to your computer probably still has all of the media files intact on it, and is only missing its index to actually locate those files.

To access the media files on the iPod directly, you must first ensure that the iPod is connected in “Disk Mode.” This is done by either preventing iTunes from opening, or preventing an automatic sync from completing, as described above. It is actually the iPod’s natural state to present itself to your computer as a removable hard disk, and is in fact only iTunes that prevents this from normally working by automatically ejecting the iPod following an automatic sync.

If you find the iPod is not staying connected, simply choose the “Enable Disk Use” option in iTunes to ensure that iTunes does not try and automatically eject the iPod for you. This option can be found by selecting the iPod in the iTunes source list, and looking on the Summary tab:

The iPod should show up in Windows Explorer or Finder (on a Mac) as a removable hard disk.

If you browse to the iPod itself, you will see a number of folders on it for some of the additional features like contacts, calendars, and notes.

What may be conspicuously absent by default, however, is the “iPod_Control” folder discussed above. This is because the iPod sets this as a “hidden” folder, which is not normally visible to the operating system.

In Windows, you can easily configure Windows Explorer to show hidden files and folders by selecting Tools, Folder Options and clicking the Show hidden files and folders item:

In Mac OS X, the process of displaying hidden files and folders is actually somewhat more complex, and requires entering commands into the “Terminal” application. To do this, open “Terminal” from under your Applications/Utilities folder, and then type in the following at the command prompt:

defaults write com.apple.finder AppleShowAllFiles TRUE

killall Finder

(Note that if you don’t know how to use “Terminal” or where to find it, you should probably stop reading this section now and skip ahead to the Third-Party Tools section, where all of these details can be easily handled for you)

Once you have typed in these commands, return to the Finder window and select your iPod from the drive listing, and you should see the iPod_Control folder:

Since viewing hidden files on Mac OS X can quickly become inconvenient, you can later turn OFF this feature by going back to Terminal and simply typing in the above two commands again, replacing the word “TRUE” with the word “FALSE.”

Once in the iPod_Control folder, you will see a number of sub-folders, including a Music folder. Despite the name, it is in this folder that all of your audio and video files actually reside. The only information that may be on your iPod that would be stored elsewhere are iPod Games and photos, which we will discuss at the end of this article.

Unfortunately, you’ll notice that the folder names and even the file names do not in any way represent the specific content.

Fortunately, however, the internal ID3 tags are still intact, so any application that can read these tags can easily sort this back out. In fact, you can take these tracks and simply reimport them directly into iTunes via the File, Add to Library option and it will happily sort them all out for you, even renaming and restructuring them in the process if you have the Keep iTunes Music folder organized setting turned on in your iTunes advanced preferences.

In fact, in a complete disaster-recovery scenario, you can even import ALL of your music files directly from the iPod itself by using the File, Add to Folder option in iTunes. To do this, you will first want to ensure that the Copy files to iTunes Music folder when adding to library option is enabled in your iTunes advanced preferences:

Once you’ve confirmed that this setting is enabled (thus ensuring that iTunes will actually copy the tracks back to your hard drive instead of referencing them directly from your iPod), you can simply select File, Add Folder to Library (Windows) or File, Add to Library (Mac) and choose the \iPod_Control\Music folder directly. iTunes will copy all of your media tracks from your iPod back to your iTunes Music Folder location, organizing them into sub-folders by ARTIST and ALBUM in the process, and naming them appropriately, all based on the internal tag information that is still stored within the files themselves.

Once your music is all safely back on your computer and imported into your iTunes library, you could then reconnect the iPod and choose the Erase and Sync option, which would erase the content from your iPod and replace it with the newly-restored content in your iTunes library.

1

Too bad it didn’t come two weeks earlier, when i myself had to rebuild my iTunes DB from my iPod as my external HDD was dead.
I successfully rebuilt the complete DB using SharePod, a MP3 Tagger and loads of time ;)

Posted by Manuel Grabowski in Toronto on July 11, 2007 at 7:32 AM (CDT)

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iPodDisk is for Mac.

On PC, your best bet is CopyTrans http://www.copytrans.net/copytrans.php as it does not only copy your songs to your computer but also all useful data such as ratings, playlists and imports all that to iTunes.

Posted by Bob1234567890 in Toronto on July 12, 2007 at 10:19 AM (CDT)

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Very good article!

I was wondering why XPlay and Anapod Explorer were not rated or mentioned?

Posted by melanchete in Toronto on July 15, 2007 at 7:01 AM (CDT)

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Although they are both excellent tools in and of themselves, XPlay and Anapod Explorer are designed as full iPod management tools to replace iTunes, and are therefore somewhat beyond the scope of this article.

Although Yamipod also provides this type of functionality, it was included due to its wide cross-platform support and its free availability.

Posted by Jesse Hollington in Toronto on July 15, 2007 at 12:39 PM (CDT)

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I’ve recently transferred my itunes music files to an external HD & have also uninstalled & reinstalled itunes. itunes can access my songs but has wiped all of the playlists, playcounts etc. I was thinking of downloading copytrans to sort this out, but is it possible to use this just to update playlists etc. or will i have to copy all of my music files & then delete the originals? Thanks for your help!

Posted by aaaaaaaaandy in Toronto on July 18, 2007 at 7:12 PM (CDT)

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My hard drive died and I am in desperate need of this article. It is not clear to me whether or not any of the software included in the article will allow you to recover videos, pictures, tv shows and games that are currently on my 30g ipod. Please help!

Posted by Middie in Toronto on July 26, 2007 at 12:21 AM (CDT)

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I get the following error when using CopyTrans. All my songs/artists/playlists show on the screen and I desperately need to copy the contents of my iPod to my itunes…ideas anyone?

System Error: 0002 ERROR_FILE_NOT_FOUND
CopyTrans Error: Source song not found on iPod.

Posted by outghost in Toronto on July 27, 2007 at 12:21 PM (CDT)

1

My iTunes doesnt have an “add to library” option. It has both “Add to Library from File” and “Add to Library from Folder”. I use iTunes 7. When I try to use the “Add from Folder” option, I get to the Ipod_Control folder and I can not go any further into it to get to the Music folder. Any ideas? Right now I’m going in to that folder from My Computer and copying all the folders into my iTunes Music folder and copying them in one folder at a time and its taking forever!!! Thanks.

Posted by givemenoise in Toronto on July 30, 2007 at 11:11 PM (CDT)

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ok, my problem is that i’m going to be moving to california in a month or so. I can take my Ipod with me but the computer is my mothers. My uncle will have a computer and I may get a laptop. I’m wondering how I can transfer my library to a different computer.

Posted by Ronaldbbbb in Toronto on August 2, 2007 at 3:03 PM (CDT)

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Hi, good article but having some small problems.

Managed to get into my ipod’s music folder, which then had a 49 F folders (ie F00 to F49) inside of which are all the music files.

Problem: my itunes is now empty. I tried ‘File Add Folder to Library’ and itunes does nothing?

I picked the entire music folder first, then tried individual F folders, and still nothing happened.

I tried this both on the copy I took of my ipod (to safeguard it in case something happened when I connected to an empty itunes and lost everything!) and also to the actual files on my ipod…

Any ideas?

Thanks - Pete

Posted by petemw2506 in Toronto on August 6, 2007 at 11:58 AM (CDT)

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Have you done any reviews on CopyGear for Mac OS X? I am wondering if this is the way to go for my new MacBook. Thanks - Jon

Posted by iJoni in Toronto on August 7, 2007 at 8:59 PM (CDT)

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Also if you have any review on iRepoX. Thanks - Jon

Posted by iJoni in Toronto on August 7, 2007 at 9:28 PM (CDT)

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I used ipod access to transfer my music from ipod to my laptop. Now I get an error message stating the majority of songs could not be used because the original file could not be found. Can I utilize this material?

Posted by scalpeldoc in Toronto on August 8, 2007 at 11:11 AM (CDT)

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my friend just bought an ipod and wants to transfer the music from my ipod to his pc. what software does he need? we have pc’s

Posted by lazysalvadorean in Toronto on August 14, 2007 at 4:55 AM (CDT)

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I have never bonded my video ipod to any machine let alone my own macbook but now i want to back up the audio files I have on the Ipod but am afraid they will get wiped when I bond my ipod to the macbook, has anyone any ideas?

Posted by anthonycronin1 in Toronto on August 15, 2007 at 12:56 PM (CDT)

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Great article! Though I didn’t make time to read it all, I don’t recall seeing any mention of having to remove the hidden attribute from the Music folder prior to trying the “Add folder to Library…” step? For iTunes 7 anyway, it wouldn’t import it with the folder properties hidden attribute set (used the Windows folder method because I don’t trust other software much).

Does anyone else think that it’s a pretty pathetic attempt to combat music/software piracy by simply using hidden folders?!? HA! What a joke…though I laugh now, I won’t be surprised if upcoming iTunes releases start using some sort of nasty algorithms or encryption. It’ll just make it harder to crack and extract.

Again, great article, a real lifesaver!

Posted by gimmie5 in Toronto on August 19, 2007 at 3:08 PM (CDT)

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FYI, for those of you who are trying the “brute-force method” of copying your media files back manually, I found that you have to make sure the folder that contains your music (the iPod_control/music folder in this article) is not a Hidden Folder. If it is, iTunes will not allow you to “Add Folder to Library.” If you right click on the folder (even in your iPod), and select Properties, you can uncheck Hidden as a property and then it should work fine. I just successfully got my entire library back!

Posted by waterguard in Toronto on August 20, 2007 at 6:09 PM (CDT)

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I have a problem still - iTunes Video library does not recognize the 20 movie files that were copied over from the iPod. I asked CopyTrans to copy ALL files and I found the movie files in the iPod Music folder.